I love it when guys wear Makeup. Lauri wears eyeshadow and eyeliner and he looks hawt.
Wear whatever you feel comfortable with Chris. I use the EXTRA FAIR foundation as Im so pale, but it works for me so I stick to it.
Its natural that your foundation will fade, mine does, but I don't bring my makeup to school. Maybe you should try concealor? It covers up blemishes and under eye bags and keeps to a natural look.